He deserves to be the most famous of all Portsmouth residents, and yet his name is still not widely known. A combination of luck and influence put a Portsmouth, NH boy from the South End smack in the heart of power at the dawn of the American nation. But each time Tobias Lear rose high on the wheel of fortune, his life soon came crashing back to earth. (Full story below)

He was technically Tobias Lear V, the fifth in his family to bear that name. Tobias Lear (1782 – 1816) was born into revolutionary times. His father's cousin John Langdon was a businessmen and privateer. A noted Portsmouth patriot, Langdon commanded the raid on FortWilliam and Mary in 1774, built two warships for naval hero John Paul Jones. attended the Continental Congress, and was an early governor of New Hampshire.

Tobias' father, who worked on the ships Ranger and Raleigh, did not fare so well. A failed shipping venture destroyed his income and created a debt that would plague his only son. His father's tombstone at Point of Graves, the one with the fearsome carving of a human skull, is just down the street from the family home on Hunking Street, now a museum. In his time, Tobias V would rise above the fame of the Langdons and fall below the debt and depression of his father.

Portsmouth Boy Makes Good

Despite moderate means, young Toby managed to attend GovernorDummerAcademy and HarvardUniversity in Massachusetts. By 1784, then in his early 20s, he was back in Portsmouth casting about for a career when a family friend received a letter from George Washington. America's "First Citizen" was in need of a private secretary, and this was no small job. A farmer by trade, General Washington had just spent a decade off fighting for the Revolution. The new secretary would have to catch up on the neglected accounting at Mt. Vernon, Washington's 10,000 acre plantation in Virginia. In addition, young Mr. Lear would become tutor to Washington's adopted children and would handle a flood of correspondence. The aristocratic "Farmer" Washington wrote to his Yankee friend describing the job this way:

"Mr. Lear...will sit at my table, will live as I live, will mix with the company who resort to the house, will be treated in every respect with civility and proper attention. He will have his washing done in the family, and may have his stockings darned by the maids..."